What a Deal! Ch. 27

Chapter 27

A reminder that this is part of a Non-Consent/Reluctance series. If you don't want to read about sex where someone is put into that position, then stop now and move on.

This is a continuation of what would be considered a "stroke" story, or as I like to call then a Jack(off) and Jill(off) story. I got some requests to continue this not very serious, fictional sex romp, so I'll try to keep up.

In the last chapter, Dennis took Jan, the wife of one of the couples from a role-playing home invasion out to a hotel, looking for a woman to fuck. It was a place known for having women looking for a hookup. They found a married one, Lucy, who wanted her husband to watch. So, Dennis took the couple upstairs where a naked Jan was waiting, and they proceeded to have a threesome while Lucy's husband Ed watched. Then Lucy came home with Dennis.

Recurring Cast

Dennis, 42 years old, 5' 11", 175 lbs, brown hair, blue eyes, Cindy's husband.

Cindy, 42 years old, 5' 4", 105 pounds, brown hair, blue eyes, Dennis' wife.

Diane, 42 years old, 5' 7", 140 lbs, auburn hair, green eyes, recently divorced friend of Cindy's.

Becky, 39 years old, 5' 9", 155 lbs, blonde hair, blue eyes, Cindy's friend, widow.

Jack, 43 years old, 6', 185 lbs, black hair, brown eyes, Louise's husband.

Louise, 39 years old, 5' 4", 130 lbs, blonde hair, brown eyes, Jack's wife.

Jackie, 20 years old, 5'6", 125 pounds, dark brown hair, blue eyes, neighbor girl.

Katy, 20 years old, 5'6", 115 pounds, blonde hair, blue eyes, Jackie's friend, now Dennis' sub.

Suzanne, 37 years old, 5'5", 125 pounds, brown hair, brown eyes, neighborhood acquaintance.

Bill, 39 years old, 5'9", 170 pounds, black hair, brown eyes, Suzanne's husband.

Brittany, 28 years old, 5'8", 120 pounds, red hair, blue eyes, Jimmy's wife.

Jimmy, 23 years old, 5'10", 160 pounds, brown hair, brown eyes, Brittany's husband.

When I woke in the morning, Lucy was lying next to me, sleeping heavily. I quietly got up and tiptoed out of the room. I was supposed to send her home full of cum, but had thought that maybe this might be a chance for some more fun with her husband Ed.

When Lucy woke up and came downstairs, she had picked up a robe. When she saw that all of us were naked, she laughed and dropped her robe.

"Hey," Lucy said. "I thought I was going to wake up to some fucking."

I laughed. "Yes, but I have a better idea that I want to work out with you. Of course, it means that Ed will get to play at being in charge. Wanna try it?"

"Maybe."

"Okay. I'll have Katy dress up in her schoolgirl uniform, albeit much sluttier than they actually wear. You take her home and act like her teacher, who saw her doing awful things and wearing no bra or panties, and wants her punished. Ed will be the principal and will take care of that. He will punish you, too, since you will also be without bra and panties. Fancy having Ed spank the two of you?"

Lucy shuddered at the thought. It sounded like something she always wanted from Ed, but was afraid to ask and he didn't bring it up. "Okay, that sounds great. Is that it?"

"Oh, no. I will call Ed, once you give me his number, and fill him in on a few details. I will also be nearby with Jan to join you guys if he asks. Okay with this?"

"Let's do it." Lucy grinned ear to ear.

I called Ed and went over the scenario.

"Lucy agreed to this? She wants to be spanked and have me role play like this?"

"Oh, yeah. She seemed rather excited by the idea, especially the spanking."

"Well, I guess I still have some things to learn about her."

"Yep."

"I want you there, too. Come in with Jan and the two of you can stay out of sight until I call you in. Okay?"

"Got it."

Ed and I then went over a few details to be on the same page.

I then ran to Jan and told her to get ready in a "teacher's outfit". But I told her to make it a dress/skirt and not to wear panties. She giggled and got ready.

I told Katy to get ready and then Jan and I left. I didn't tell Lucy that we'd actually be there.

Jan and I arrived and Ed immediately let us in. He was in business casual and took us into one of the bedrooms just off the hallway. We would be able to creep down the hallway and watch once things got going.

About 5 minutes later, Lucy and Katy arrived. Ed answered the door and had made up a name for Lucy.

Ed immediately went into his role as he led them over near the dining room table. "Ah, Mrs. Wilson. I see you brought the girl you said was unruly. What is it that she has done that has gotten you so upset and made you bring her to me for punishment?"

"Well, sir, she was parading around in this outfit," she waved her hand at Katy's very short tartan skirt and braless and partially opened white shirt, "and when she would twirl, the boys were all making comments and I realized she is not wearing panties. She was showing everyone her privates."

Ed looked at her. "You mean she was flashing her ass and pussy?"

"Uh, yes, sir." Lucy tried to look shocked by those words.

Jan and I had crept down the hall and watched closely to see if Ed could pull this off.

"Katy! Get over here." Ed was standing by the dining room table, which he had moved to face the room like it was a large desk. On it he had placed a folded piece of paper with the name "Mr. Smith". Katy moved over to him, staring at her shoes as if she didn't want to look him in the eyes. "Why were you acting like such a slut? Don't you know that for the rest of their lives, those boys will look at you and think 'slut'?"

"I guess so, Mr. Smith."

"As a man, I can promise you that it's true. Now, as you well know, this school has a policy that says that all women and young ladies must wear undergarments, both a bra and panties. So, as your punishment, I am going to give you ten swats on the ass. Do you agree with this punishment?"

"Yes, sir," Katy said meekly.

"Come right here." Ed patted the table right in front of him. "I want you to take one step back from the table and then bend over and put your arms on it from the elbows to your hands."

Katy did so, and as she did, her skirt rode up dangerously close to showing her ass and pussy. It was very short for the school standard.

Ed looked up at Lucy. "Mrs. Wilson, please lift Katy's skirt up over her back."

Lucy stepped forward and did so. She started to step away, but Ed grabbed her by the arm. He put her by his side.

"Stay right here, Mrs. Wilson, and pay attention to the punishment."

Ed put his hand on Katy's ass. "As you can see, Mrs. Wilson, this is a fine young ass. It's no wonder the boys were so interested in it. Now, for the punishment."

Ed took his right hand and brought it back and down on her right cheek. It was of medium strength, but still startled Katy and she let out a squeak. Ed then did the left cheek. He repeated these two more times for six swats on her ass, three on each side.

Ed stopped and left his hand on Katy's ass. "Yes, this is working well. You can feel the heat and see how her ass is turning a little red, pushing the blood to the surface. See that, Mrs. Wilson?"

"Yes, sir."

Ed rubbed his hand around Katy's ass, feeling not just the heat, but enjoying his chance to feel a beautiful young ass. He turned to Lucy and grinned.

Ed reached over and grabbed Lucy's right hand. "Here, I want you to feel this." Ed took Lucy's right hand and laid it on Katy's right cheek. She let him. "Feel that heat?" He grinned at Lucy. Lucy tried to act a little hesitant, but she knew his game was to entice her to play with Katy, so she helped him by moving her hand slightly over Katy's ass.

Ed released her hand and watched her rub Katy's ass. "I see you like the feel of a reddened ass."

Lucy jerked her hand back. "No, sir. I was -- uh -- just -- uh -- distracted."

Ed grinned. He stepped back and pulled Lucy in front of him in the position where he had been giving the spanking. "I think you like this idea. I want you to take the last four swats."

"No, that's okay, Mr. Smith. You must administer the punishments."

"Nonsense. As a teacher who may want to become a principal one day, you need to learn this. Now, take your right hand and lay it on her ass where you want to hit. Okay, good. Now, feel the heat and run your hand over her entire ass. Nice. Okay, when you are ready, give her a swat on each side."

Lucy had started running her hand over Katy's ass and it appeared that she loved this idea. She was being directed to spank and play with a very young lady by her husband.

Lucy, as Mrs. Wilson, suddenly pulled her hand back and smacked Katy's ass on the right cheek. She ran her hand all over that nice ass and then did the same to the left. She was running her hand over the ass again when Ed stepped up and stopped her by grabbing her wrist.

"Now, I think we are administering a punishment, but Katy seems to be enjoying it a little too much, don't you think?"

Lucy looked down at the red ass and then back and Ed. "How do you know?"

Ed grinned at her attempt at naivete. "Feel her pussy and see if it is swollen and wet."

Lucy stared down at the ass. She was enjoying this, but wanted Ed to make her do each step as Mrs. Wilson. "Uhhh, I don't know if I can."

"Of course, you can. This is just to see if she is enjoying being spanked. Here, I'll help you."

This is just what Lucy wanted. Ed took her hand and guided it down Katy's ass crack and onto her pussy. Katy was actually soaking wet. She really was enjoying this entire scenario. Lucy was turned on, too, and knew that a check of her pussy would show her just as wet.

Ed moved her hand back and forth over Katy's pussy and then brought her hand up towards their faces. He leaned over and took a deep breath. "Yep, that's a nice, wet pussy smell. Let's see how it tastes." Ed then bent over and took one of Lucy's fingers into his mouth. She started a little, as this was really getting to her.

Ed grinned at Lucy and guided one of her other wet fingers toward her mouth. He stared into her eyes and waited for her to open her mouth. She finally did and he moved that finger into it. He grinned as Lucy sucked on it.

I thought this was going very well. Everyone was playing their role perfect. There was some hesitation to try to make it real, but eventually they gave in to Ed's fantasy.

Now Ed pressed up behind Lucy and made sure he had rearranged his cock to fit right along the crack of her ass. He wiggled his hips to accentuate what he had done. Lucy moaned a little, but was back to administering the punishment to Katy. She gave her the ninth and ten spanks, on her right and left cheeks, respectively.

Then Ed took Lucy's hand again. This time he specifically took two fingers and ran them down over Katy's ass and actually partially into her pussy. He grinned and lightly dry-humped Lucy. I looked at Jan next to me and she was practically drooling.

Ed took Lucy's hand and brought it up to her mouth. She immediately started sucking on the two fingers.

Ed whispered in Lucy's ear, just loud enough for us to hear, "You like licking those pussy juices off your finger, don't you?" Lucy hesitated and then nodded. "And you like it when I push my cock up against your ass, right?" Lucy nodded again.

Katy was looking over her shoulder and grinning. Ed, meanwhile, had taken his other hand and run it up under Lucy's dress.

"Mrs. Wilson!" Ed suddenly exclaimed. "You are not wearing undergarments!"

Lucy hung her head in mock embarrassment. "I'm sorry, sir."

"I was just giving a student punishment for this and you, her teacher, who brought her to me, is violating the same policy?" Ed stepped back from her. "Katy, stand up." Ed looked her up and down and moved forward and put his hand into her shirt. "You are not wearing a bra. I didn't ask that at first, but now that I have, you must remove your shirt, too." Katy grinned as she did so. Ed looked her young and fit body up and down. Then he turned to Lucy.

Ed lifted her skirt up enough to see her pussy. "No panties." He then felt up her tits through her blouse. "And no bra. You both completely violated this school policy. Mrs. Wilson, please remove your blouse and bend over the desk. You will also receive 10 swats for this violation. Understood?"

"Yes, sir." Lucy removed her blouse, displaying her firm tits.

Ed stared at them. "Very nice, Mrs. Wilson. I'm sure Mr. Wilson enjoys them very much." Ed grinned and then held his hand up. He made the sign with his index finger for turn around. Lucy did, and then bent over the makeshift desk. "Now, I'm going to drape your skirt up over your back to give me access to that bare ass that is going to get spanked." He did that and then turned to Katy, who was still standing there. "I want you to get back in your original position, spanking or not." She did.

Ed put his hand on Lucy's ass. He ran his hand all over her ass, which was a very nice, tight ass. He then quickly brought it up and away and back down. The smack was loud because of the flat contact of his hand. Lucy let out a squeak, but tried to stay quiet. Ed quickly gave her the first six, just like he did with Katy. Now he slowed down and looked over at me. He gave me the thumbs up, which was our sign for me and Jan to come barging in.

I looked at Jan and she looked like she was ready to fuck already. She was turned on watching these two get spanked and played with in this role play way by Ed.

We stood up and walked into the room. As soon as the others heard our footsteps, I announced our presence. "Hello Mr. Smith, I see there are punishments already ongoing here."

Katy and Lucy both were surprised by this turn of events and rose up, covered their asses, and looked over our shoulders at us. I could see both of them smile a bit when they saw who it was. They had to know that something had been planned when they saw me.

Ed waved his hand at the two bare-assed women. "Yes, Mr. Jones, there were some clothing violations today, so I was conducting punishment on these two. This," he pointed at Katy, "is Miss Katy Vincent. And this," he pointed at Lucy, "is Mrs. Wilson, a teacher. They both violated the school policy about wearing undergarments. As a matter of fact, neither one was wearing a bra or panties."

I nodded knowingly. "Well, there is another punishment required." I had briefed Jan on this and had pulled her into the room by her arm, with her slightly protesting. "This is Mrs. Taylor. She's the new librarian. I found her in the library with no undergarments on as she had one hand in her blouse rubbing her tits and one under her skirt playing with her pussy while watching porn on a school computer."

Ed shook his head gravely. "That just will not do, Mrs. Taylor. You will have to be punished alongside these two strumpets."

Jan looked at them and tried to look scared, but she was not doing well. She looked like she wanted to kneel behind them and lick their pussies.

Ed took over, as I suggested he do. "Well, Mrs. Taylor come over here. When violating the school policy, you must remove the outer garment that shows the missing undergarment. So please remove your blouse and bend over the table so that you can receive your punishment. It is usually ten swats with a bare hand. Do you agree with this punishment?"

Jan grimaced. "And if I don't' agree?"

Ed nodded. "Then you are welcome to seek employment elsewhere."

Jan nodded. "Okay." She removed her blouse and her really nice tits came into view. She was a little fleshier than the other two, who were more the tight, fit ones. Jan then went to the table where Ed was pointing and looked at the other two. They looked back and nodded like people bonding over a common shared event.

Ed had pointed to the right of Lucy, which I thought was a mistake. He is right-handed and I thought that meant that he wouldn't be able to watch my interaction with his wife. He had said he was going to push her, so I was wondering exactly what that meant. But then Ed went to the far side of Jan and grinned at me.

"I'm ambidextrous when it comes to this."

I grinned. "Okay, so where are we in the punishments."

"Well, Katy has received her spanking. Mrs. Wilson has had 6 swats of her ten and needs four more, plus some stimulation. I will start Mrs. Taylor now."

Ed put his hand on Jan's ass. He immediately gave her two quick swats, one on each cheek. "This is a nice ass, too, Mrs. Taylor. I'm sure your husband enjoys spanking it."

"He doesn't spank me."

"Shame." Ed ran his hand through her dripping pussy. "You seem to like the idea quite a lot." And with that Ed smacked her on the right cheek. Then immediately on the left cheek. He then ran his hand all over her ass. "So smooth and spankable. One of the best asses I've seen."

Ed ran his hand over her ass, from one check to the other, savoring the flesh. Then he gave her another quick swat on both cheeks. "Now, for many people there is a point at which pleasure and pain can be blurred. I think that the Vice-Principal and I will demonstrate."

When he said that I pulled Katy back and handed her my phone. She grinned and moved to directly behind the two beautiful and fuckable asses on display.

"Ready, Mr. Jones?"

"Of course."

Ed then put his left hand on Jan's ass and when he pulled his hand back to spank her, he reached under and started playing with her tits. He smacked her as he was rubbing the nipple on her right tit. She moaned. Then Ed spanked her other cheek while continuing to stimulate her tits, his hands running back and forth over the dangling globes of flesh and scraping across her nipples. Jan moaned some more.

"Now you try it Mr. Jones."

I gave Katy a come hither with a nod of my head and whispered to her to take down our pants while we were doing this. She started with Ed.

I put my hand under Lucy and started rubbing her tits. She pressed down into my hand and I smacked her left cheek. "Seven." Lucy just kept squirming as I mauled her tits. Then I hit her on the right cheek. "Eight." Lucy continued to moan and squirm.

Katy had gotten both our pants down and our cocks stood straight out.

"Very nice, Mr. Jones. Now, these last two for each of you will be accomplished with a different form of pain and pleasure." Ed and I moved behind our respective miscreants and when we were both ready, Ed nodded to me and we both started working on getting our cocks into the very wet pussies in front of us.

Both Lucy (Mrs. Wilson) and Jan (Mrs. Taylor) started to stand up. Both Ed and I pushed down on their shoulders.

Ed said, "We are not finished with your punishments, ladies. You must submit to the complete punishment or we'll have to start again."

Lucy groaned. "But, Mr. Smith, I am not on birth control and my husband and I are trying to have a baby. Mr. Jones is not wearing a condom."

Ed grinned at me. His wife was really enjoying the role playing. "Mrs. Wilson, calm down. Mr. Jones is not going to cum in you while we are spanking you. He merely needs to demonstrate the close connection between pain and pleasure to you. We will be done in just a couple of swats."

The two ladies seemed to relent, so Ed and I started fucking them. After about 10 strokes, Ed smacked Jan on the right check. "Nine."

I followed on Lucy.

Then Ed struck her on the left and said, "Ten." He then pulled out of her, his cock glistening with her juices.

I followed suit and pulled out, also with a hard, wet cock.

Both Lucy and Jan groaned when we stopped.

"Is there something else, ladies?" Ed asked them while rubbing both asses. "Are you too turned on to leave? Do you need to cum right now?"

They both groaned a yes and then stood up.

Ed kept going. "Okay, Mrs. Taylor, come lay down here on the nice shag throw rug." Jan scrambled to do so. "Mrs. Wilson, please take a 69 position over Mrs. Taylor." She did so, as well.